Wing half Valentine Francis Gregory was born on St Valentine’s Day 1888 at Hendon, Middlesex, and first started playing football for local junior sides Shepherds Bush, Pinner, Harefield United, Wealdstone and Northwood Wednesday. He joined Southern League Reading as an amateur in 1910 without making their first eleven, but soon moved to sign for local club Watford in 1911 at about the same time as three of his brothers, Allan, Owen and older brother Fred also joined Watford, both Fred and Val turning professional in November 1911. Fred would go on to play more than 300 games for Watford through till 1926.
Val Gregory made his Southern League debut in a 1-1 draw at Luton Town on Christmas Day 1911, going on to score 16 goals in 161 appearances for Watford. Both brothers were key to Watford winning the 1914-15 Southern League Championship, Val being ever present during the campaign.
During the First World War he played 41 wartime games for Watford, scoring once. He also made a guest appearance for Arsenal during the War, and continued to play for The Hornets after the resumption of peacetime football in 1919, Watford finishing Southern League runners up to Portsmouth narrowly on goal average in 1919-20.
In May 1920 he signed for Second Division Wolverhampton Wanderers for £1,500, at the time a Watford club record transfer fee, joining Wolves along with team mate George Edmunds, the top scorer from the title-winning season. He became Wolves’ Club Captain and in his first season led them on an 8 game FA Cup odyssey culminating in the 1921 FA Cup Final which they narrowly lost 1-0 to Jimmy Dimmock’s second half winner for Tottenham Hotspur at Stamford Bridge. Gregory played 106 games for Wolves scoring twice over three seasons at Molineux, making his final appearance against Crystal Palace in May 1923 at the end of what was a relegation season for Wolves. He finished his playing days as an amateur for Butler Sports and Wolverhampton Football Club before joining the Wolves coaching staff in 1925, remaining there until 1938.